CA1211470A - Process for the preparation of anilines substituted in the meta-position(s) by chlorine - Google Patents

Process for the preparation of anilines substituted in the meta-position(s) by chlorine

Info

Publication number: CA1211470A
Authority: CA; Canada
Prior art keywords: process according; chlorine; reaction; carried out; atom
Prior art date: 1980-08-01
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000382858A

Other languages

English (en)

French (fr)

Inventor

Georges Cordier

Pierre Fouilloux

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer CropScience SA

Original Assignee

Rhone Poulenc Agrochimie SA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-08-01

Filing date

1981-07-30

Publication date

1986-09-16

1980-08-01 Priority claimed from FR8017324A external-priority patent/FR2487823A1/fr

1980-09-26 Priority claimed from FR8020979A external-priority patent/FR2491059A2/fr

1981-07-30 Application filed by Rhone Poulenc Agrochimie SA filed Critical Rhone Poulenc Agrochimie SA

1986-09-16 Application granted granted Critical

1986-09-16 Publication of CA1211470A publication Critical patent/CA1211470A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 40
229910052801 chlorine Inorganic materials 0.000 title claims abstract description 26
239000000460 chlorine Substances 0.000 title claims abstract description 13
238000002360 preparation method Methods 0.000 title claims abstract description 11
150000001448 anilines Chemical group 0.000 title claims abstract description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 title claims abstract description 5
238000006243 chemical reaction Methods 0.000 claims abstract description 36
239000003054 catalyst Substances 0.000 claims abstract description 26
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 21
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 18
239000002841 Lewis acid Substances 0.000 claims abstract description 13
150000007517 lewis acids Chemical class 0.000 claims abstract description 13
229910000510 noble metal Inorganic materials 0.000 claims abstract description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 7
239000007791 liquid phase Substances 0.000 claims abstract description 6
150000005181 nitrobenzenes Chemical class 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
230000003197 catalytic effect Effects 0.000 claims abstract description 5
230000000737 periodic effect Effects 0.000 claims abstract description 5
PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 claims abstract description 4
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 4
238000009903 catalytic hydrogenation reaction Methods 0.000 claims abstract description 3
125000003710 aryl alkyl group Chemical group 0.000 claims abstract 4
125000003118 aryl group Chemical group 0.000 claims abstract 4
125000004104 aryloxy group Chemical group 0.000 claims abstract 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 22
UQRLKWGPEVNVHT-UHFFFAOYSA-N 3,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1 UQRLKWGPEVNVHT-UHFFFAOYSA-N 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
229910052763 palladium Inorganic materials 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 10
PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Substances Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 claims description 9
GBKZRUCVLTWAML-UHFFFAOYSA-N 2,3,4,5-tetrachloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C(Cl)=C1Cl GBKZRUCVLTWAML-UHFFFAOYSA-N 0.000 claims description 8
XOGYQVITULCUGU-UHFFFAOYSA-N 3,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C(Cl)=C1 XOGYQVITULCUGU-UHFFFAOYSA-N 0.000 claims description 8
UAYWVJHJZHQCIE-UHFFFAOYSA-L Zinc iodide Inorganic materials I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 claims description 8
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
239000012429 reaction media Substances 0.000 claims description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
YTDHEFNWWHSXSU-UHFFFAOYSA-N 2,3,5,6-tetrachloroaniline Chemical compound NC1=C(Cl)C(Cl)=CC(Cl)=C1Cl YTDHEFNWWHSXSU-UHFFFAOYSA-N 0.000 claims description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
229910052782 aluminium Inorganic materials 0.000 claims description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
229910052797 bismuth Inorganic materials 0.000 claims description 3
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 3
150000001805 chlorine compounds Chemical class 0.000 claims description 3
229910052718 tin Inorganic materials 0.000 claims description 3
BGKIECJVXXHLDP-UHFFFAOYSA-N 1,2,3-trichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1Cl BGKIECJVXXHLDP-UHFFFAOYSA-N 0.000 claims description 2
HHLCSFGOTLUREE-UHFFFAOYSA-N 1,2,3-trichloro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C(Cl)=C1 HHLCSFGOTLUREE-UHFFFAOYSA-N 0.000 claims description 2
IBRBMZRLVYKVRF-UHFFFAOYSA-N 1,2,4-trichloro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C=C1Cl IBRBMZRLVYKVRF-UHFFFAOYSA-N 0.000 claims description 2
ZYJBTGNUWOMRBG-UHFFFAOYSA-N 1,2,5-trichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(Cl)=C1Cl ZYJBTGNUWOMRBG-UHFFFAOYSA-N 0.000 claims description 2
CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 claims description 2
NTBYINQTYWZXLH-UHFFFAOYSA-N 1,2-dichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1 NTBYINQTYWZXLH-UHFFFAOYSA-N 0.000 claims description 2
RZKKOBGFCAHLCZ-UHFFFAOYSA-N 1,4-dichloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1Cl RZKKOBGFCAHLCZ-UHFFFAOYSA-N 0.000 claims description 2
KHCZSJXTDDHLGJ-UHFFFAOYSA-N 2,3,4,5,6-pentachloroaniline Chemical compound NC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl KHCZSJXTDDHLGJ-UHFFFAOYSA-N 0.000 claims description 2
LXCLPHJRGDTDDB-UHFFFAOYSA-N 2,3,4,6-tetrachloroaniline Chemical compound NC1=C(Cl)C=C(Cl)C(Cl)=C1Cl LXCLPHJRGDTDDB-UHFFFAOYSA-N 0.000 claims description 2
RRJUYQOFOMFVQS-UHFFFAOYSA-N 2,3,4-trichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1Cl RRJUYQOFOMFVQS-UHFFFAOYSA-N 0.000 claims description 2
MOTBXEPLFOLWHZ-UHFFFAOYSA-N 2,3,5-trichloroaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1Cl MOTBXEPLFOLWHZ-UHFFFAOYSA-N 0.000 claims description 2
BRPSAOUFIJSKOT-UHFFFAOYSA-N 2,3-dichloroaniline Chemical compound NC1=CC=CC(Cl)=C1Cl BRPSAOUFIJSKOT-UHFFFAOYSA-N 0.000 claims description 2
GUMCAKKKNKYFEB-UHFFFAOYSA-N 2,4,5-trichloroaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1Cl GUMCAKKKNKYFEB-UHFFFAOYSA-N 0.000 claims description 2
AVYGCQXNNJPXSS-UHFFFAOYSA-N 2,5-dichloroaniline Chemical compound NC1=CC(Cl)=CC=C1Cl AVYGCQXNNJPXSS-UHFFFAOYSA-N 0.000 claims description 2
SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 claims description 2
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 2
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
229910021586 Nickel(II) chloride Inorganic materials 0.000 claims description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
VNDYJBBGRKZCSX-UHFFFAOYSA-L Zinc bromide Inorganic materials Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 2
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims description 2
239000004411 aluminium Substances 0.000 claims description 2
229910052787 antimony Inorganic materials 0.000 claims description 2
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
229910052785 arsenic Inorganic materials 0.000 claims description 2
RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 2
229910052796 boron Inorganic materials 0.000 claims description 2
229910052793 cadmium Inorganic materials 0.000 claims description 2
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 2
229910017052 cobalt Inorganic materials 0.000 claims description 2
239000010941 cobalt Substances 0.000 claims description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
239000010949 copper Substances 0.000 claims description 2
OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 2
229910052733 gallium Inorganic materials 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
229910052750 molybdenum Inorganic materials 0.000 claims description 2
239000011733 molybdenum Substances 0.000 claims description 2
229910052759 nickel Inorganic materials 0.000 claims description 2
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
LKPLKUMXSAEKID-UHFFFAOYSA-N pentachloronitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LKPLKUMXSAEKID-UHFFFAOYSA-N 0.000 claims description 2
229910052698 phosphorus Inorganic materials 0.000 claims description 2
239000011574 phosphorus Substances 0.000 claims description 2
XQTLDIFVVHJORV-UHFFFAOYSA-N tecnazene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl XQTLDIFVVHJORV-UHFFFAOYSA-N 0.000 claims description 2
229910052719 titanium Inorganic materials 0.000 claims description 2
239000010936 titanium Substances 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
239000011701 zinc Substances 0.000 claims description 2
239000011592 zinc chloride Substances 0.000 claims description 2
235000005074 zinc chloride Nutrition 0.000 claims description 2
229910052726 zirconium Inorganic materials 0.000 claims description 2
239000007858 starting material Substances 0.000 claims 2
MTBYTWZDRVOMBR-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C(Cl)=C1Cl MTBYTWZDRVOMBR-UHFFFAOYSA-N 0.000 claims 1
LOCIEHQKRSFTPA-UHFFFAOYSA-N 1,2,3,5-tetrachloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C=C(Cl)C(Cl)=C1Cl LOCIEHQKRSFTPA-UHFFFAOYSA-N 0.000 claims 1
UDEAXERKYRDHTE-UHFFFAOYSA-N 1,2,4-trichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C=CC(Cl)=C1Cl UDEAXERKYRDHTE-UHFFFAOYSA-N 0.000 claims 1
ZJMMPUVJZQBMEM-UHFFFAOYSA-N 2,3,6-trichloroaniline Chemical compound NC1=C(Cl)C=CC(Cl)=C1Cl ZJMMPUVJZQBMEM-UHFFFAOYSA-N 0.000 claims 1
229940045803 cuprous chloride Drugs 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract description 2
239000004476 plant protection product Substances 0.000 abstract description 2
125000000547 substituted alkyl group Chemical group 0.000 abstract 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
-1 alkyl radical Chemical class 0.000 description 7
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
239000012071 phase Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
239000000243 solution Substances 0.000 description 4
PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
JKMPXGJJRMOELF-UHFFFAOYSA-N 1,3-thiazole-2,4,5-tricarboxylic acid Chemical compound OC(=O)C1=NC(C(O)=O)=C(C(O)=O)S1 JKMPXGJJRMOELF-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
238000005260 corrosion Methods 0.000 description 3
230000007797 corrosion Effects 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
229910052709 silver Inorganic materials 0.000 description 3
239000004332 silver Substances 0.000 description 3
BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
150000005840 aryl radicals Chemical class 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000007789 gas Substances 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
DQNOIKMHTBFYTD-UHFFFAOYSA-N n,n,2,3-tetrachloroaniline Chemical compound ClN(Cl)C1=CC=CC(Cl)=C1Cl DQNOIKMHTBFYTD-UHFFFAOYSA-N 0.000 description 2
KUDPGZONDFORKU-UHFFFAOYSA-N n-chloroaniline Chemical group ClNC1=CC=CC=C1 KUDPGZONDFORKU-UHFFFAOYSA-N 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical class [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
RWGZRRPLEGKJDN-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5-methoxy-6-nitrobenzene Chemical compound COC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1[N+]([O-])=O RWGZRRPLEGKJDN-UHFFFAOYSA-N 0.000 description 1
CWEVPIBZXIZFLU-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5-nitro-6-phenoxybenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1OC1=CC=CC=C1 CWEVPIBZXIZFLU-UHFFFAOYSA-N 0.000 description 1
YARSGRBMBZVXCZ-UHFFFAOYSA-N 1,2,3,5-tetrachloro-4-nitro-6-phenoxybenzene Chemical compound [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C(OC=2C=CC=CC=2)=C1Cl YARSGRBMBZVXCZ-UHFFFAOYSA-N 0.000 description 1
NQEKOOGCLIIIKC-UHFFFAOYSA-N 1,2,3-trichloro-4-methoxy-5-nitrobenzene Chemical compound COC1=C(Cl)C(Cl)=C(Cl)C=C1[N+]([O-])=O NQEKOOGCLIIIKC-UHFFFAOYSA-N 0.000 description 1
WMTUZUWHSNEAQO-UHFFFAOYSA-N 1,2,3-trichloro-4-nitro-5-phenylbenzene Chemical group [O-][N+](=O)C1=C(Cl)C(Cl)=C(Cl)C=C1C1=CC=CC=C1 WMTUZUWHSNEAQO-UHFFFAOYSA-N 0.000 description 1
WDIKVKQUYUJSQS-UHFFFAOYSA-N 1,2,3-trichloro-5-methyl-4-nitrobenzene Chemical compound CC1=CC(Cl)=C(Cl)C(Cl)=C1[N+]([O-])=O WDIKVKQUYUJSQS-UHFFFAOYSA-N 0.000 description 1
WELCXTXFMAVVKR-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-nitro-6-phenoxybenzene Chemical compound ClC1=C(Cl)C([N+](=O)[O-])=C(Cl)C(Cl)=C1OC1=CC=CC=C1 WELCXTXFMAVVKR-UHFFFAOYSA-N 0.000 description 1
DKUDFGKZVHDKGG-UHFFFAOYSA-N 1,2,5-trichloro-3-methoxy-4-nitrobenzene Chemical compound COC1=C(Cl)C(Cl)=CC(Cl)=C1[N+]([O-])=O DKUDFGKZVHDKGG-UHFFFAOYSA-N 0.000 description 1
YBCSBMLIXWHLQI-UHFFFAOYSA-N 1,2-dichloro-3-methoxy-4-nitrobenzene Chemical compound COC1=C(Cl)C(Cl)=CC=C1[N+]([O-])=O YBCSBMLIXWHLQI-UHFFFAOYSA-N 0.000 description 1
LYFAMXRWZNBHLH-UHFFFAOYSA-N 1,2-dichloro-3-methoxy-5-nitrobenzene Chemical compound COC1=CC([N+]([O-])=O)=CC(Cl)=C1Cl LYFAMXRWZNBHLH-UHFFFAOYSA-N 0.000 description 1
BHJTYLCUHUTYEE-UHFFFAOYSA-N 1,2-dichloro-4-methoxy-3-nitrobenzene Chemical compound COC1=CC=C(Cl)C(Cl)=C1[N+]([O-])=O BHJTYLCUHUTYEE-UHFFFAOYSA-N 0.000 description 1
QFQSBAMTGUKFKS-UHFFFAOYSA-N 1,2-dichloro-4-methoxy-5-nitrobenzene Chemical compound COC1=CC(Cl)=C(Cl)C=C1[N+]([O-])=O QFQSBAMTGUKFKS-UHFFFAOYSA-N 0.000 description 1
LBKQVYCKFHARBV-UHFFFAOYSA-N 1,2-dichloro-4-nitro-5-phenoxybenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C=C1OC1=CC=CC=C1 LBKQVYCKFHARBV-UHFFFAOYSA-N 0.000 description 1
KTPPCTQPGJFQHB-UHFFFAOYSA-N 1,2-dichloro-5-methoxy-3-nitrobenzene Chemical compound COC1=CC(Cl)=C(Cl)C([N+]([O-])=O)=C1 KTPPCTQPGJFQHB-UHFFFAOYSA-N 0.000 description 1
WRSWHUVIGGFTNU-UHFFFAOYSA-N 1,3,4-trichloro-2-methoxy-5-nitrobenzene Chemical compound COC1=C(Cl)C=C([N+]([O-])=O)C(Cl)=C1Cl WRSWHUVIGGFTNU-UHFFFAOYSA-N 0.000 description 1
SHUMTDRNPCDTCO-UHFFFAOYSA-N 1,3,4-trichloro-5-methoxy-2-nitrobenzene Chemical compound COC1=CC(Cl)=C([N+]([O-])=O)C(Cl)=C1Cl SHUMTDRNPCDTCO-UHFFFAOYSA-N 0.000 description 1
WFWQRAOIFLTRMH-UHFFFAOYSA-N 1,4-dichloro-2,3-dimethyl-5-nitrobenzene Chemical compound CC1=C(C)C(Cl)=C([N+]([O-])=O)C=C1Cl WFWQRAOIFLTRMH-UHFFFAOYSA-N 0.000 description 1
DVGWQGRGSAQPQJ-UHFFFAOYSA-N 1,4-dichloro-2-methoxy-5-nitrobenzene Chemical compound COC1=CC(Cl)=C([N+]([O-])=O)C=C1Cl DVGWQGRGSAQPQJ-UHFFFAOYSA-N 0.000 description 1
PEQYJEJKUTUIFJ-UHFFFAOYSA-N 1,4-dichloro-2-methyl-5-nitrobenzene Chemical compound CC1=CC(Cl)=C([N+]([O-])=O)C=C1Cl PEQYJEJKUTUIFJ-UHFFFAOYSA-N 0.000 description 1
ZZHOGSARBSKHBZ-UHFFFAOYSA-N 1,4-dichloro-2-nitro-5-phenoxybenzene Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(Cl)=C1OC1=CC=CC=C1 ZZHOGSARBSKHBZ-UHFFFAOYSA-N 0.000 description 1
IIHRBBRFSOLMCD-UHFFFAOYSA-N 1,4-dichloro-2-nitro-5-propylbenzene Chemical compound CCCC1=CC(Cl)=C([N+]([O-])=O)C=C1Cl IIHRBBRFSOLMCD-UHFFFAOYSA-N 0.000 description 1
ONRFSTKRXHVKTI-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-methoxyaniline Chemical compound COC1=C(N)C(Cl)=C(Cl)C(Cl)=C1Cl ONRFSTKRXHVKTI-UHFFFAOYSA-N 0.000 description 1
ZUMRAASOHVUGRC-UHFFFAOYSA-N 2,3,4,5-tetrachloro-6-phenoxyaniline Chemical compound NC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1OC1=CC=CC=C1 ZUMRAASOHVUGRC-UHFFFAOYSA-N 0.000 description 1
QDRIOLWGEOQJCP-UHFFFAOYSA-N 2,3,4,6-tetrachloro-5-methoxyaniline Chemical compound COC1=C(Cl)C(N)=C(Cl)C(Cl)=C1Cl QDRIOLWGEOQJCP-UHFFFAOYSA-N 0.000 description 1
AMKZKITUPXRCRX-UHFFFAOYSA-N 2,3,4,6-tetrachloro-5-phenoxyaniline Chemical compound NC1=C(Cl)C(Cl)=C(Cl)C(OC=2C=CC=CC=2)=C1Cl AMKZKITUPXRCRX-UHFFFAOYSA-N 0.000 description 1
WUIMAOZZLPNIMF-UHFFFAOYSA-N 2,3,4-trichloro-5-methoxyaniline Chemical compound COC1=CC(N)=C(Cl)C(Cl)=C1Cl WUIMAOZZLPNIMF-UHFFFAOYSA-N 0.000 description 1
FBHJFDRYHRDILH-UHFFFAOYSA-N 2,3,4-trichloro-6-methylaniline Chemical compound CC1=CC(Cl)=C(Cl)C(Cl)=C1N FBHJFDRYHRDILH-UHFFFAOYSA-N 0.000 description 1
VPAUYXVZVIXQBZ-UHFFFAOYSA-N 2,3,4-trichloro-6-phenylaniline Chemical group NC1=C(Cl)C(Cl)=C(Cl)C=C1C1=CC=CC=C1 VPAUYXVZVIXQBZ-UHFFFAOYSA-N 0.000 description 1
MBYRIGCRDZOZTI-UHFFFAOYSA-N 2,3,5,6-tetrachloro-4-methoxyaniline Chemical compound COC1=C(Cl)C(Cl)=C(N)C(Cl)=C1Cl MBYRIGCRDZOZTI-UHFFFAOYSA-N 0.000 description 1
MVLQHKBMRKTIOB-UHFFFAOYSA-N 2,3,5-trichloro-4-methoxyaniline Chemical compound COC1=C(Cl)C=C(N)C(Cl)=C1Cl MVLQHKBMRKTIOB-UHFFFAOYSA-N 0.000 description 1
GMXFJTFHFYKUQF-UHFFFAOYSA-N 2,3,6-trichloro-4-methoxyaniline Chemical compound COC1=CC(Cl)=C(N)C(Cl)=C1Cl GMXFJTFHFYKUQF-UHFFFAOYSA-N 0.000 description 1
JXWUMFLJRZJKAZ-UHFFFAOYSA-N 2,3-dichloro-1-methoxy-4-nitrobenzene Chemical compound COC1=CC=C([N+]([O-])=O)C(Cl)=C1Cl JXWUMFLJRZJKAZ-UHFFFAOYSA-N 0.000 description 1
LZYMHTVWOMZPEO-UHFFFAOYSA-N 2,3-dichloro-4-methoxyaniline Chemical compound COC1=CC=C(N)C(Cl)=C1Cl LZYMHTVWOMZPEO-UHFFFAOYSA-N 0.000 description 1
CNMBMHIFTUIKLJ-UHFFFAOYSA-N 2,3-dichloro-5-methoxyaniline Chemical compound COC1=CC(N)=C(Cl)C(Cl)=C1 CNMBMHIFTUIKLJ-UHFFFAOYSA-N 0.000 description 1
NGQZFSHSIJZJNX-UHFFFAOYSA-N 2,3-dichloro-6-methoxyaniline Chemical compound COC1=CC=C(Cl)C(Cl)=C1N NGQZFSHSIJZJNX-UHFFFAOYSA-N 0.000 description 1
NJZMXYAVRVWZAS-UHFFFAOYSA-N 2,5-dichloro-1-methoxy-3-nitrobenzene Chemical compound COC1=CC(Cl)=CC([N+]([O-])=O)=C1Cl NJZMXYAVRVWZAS-UHFFFAOYSA-N 0.000 description 1
MRDOLSVLOGGRAE-UHFFFAOYSA-N 2,5-dichloro-3,4-dimethylaniline Chemical compound CC1=C(C)C(Cl)=C(N)C=C1Cl MRDOLSVLOGGRAE-UHFFFAOYSA-N 0.000 description 1
JHZWCHORDSEJQD-UHFFFAOYSA-N 2,5-dichloro-3-methoxyaniline Chemical compound COC1=CC(Cl)=CC(N)=C1Cl JHZWCHORDSEJQD-UHFFFAOYSA-N 0.000 description 1
DKLUBYIAONUMRE-UHFFFAOYSA-N 2,5-dichloro-4-ethylaniline Chemical compound CCC1=CC(Cl)=C(N)C=C1Cl DKLUBYIAONUMRE-UHFFFAOYSA-N 0.000 description 1
VCMXIPGKIUDONN-UHFFFAOYSA-N 2,5-dichloro-4-methoxyaniline Chemical compound COC1=CC(Cl)=C(N)C=C1Cl VCMXIPGKIUDONN-UHFFFAOYSA-N 0.000 description 1
QXDILMJTDWNTAV-UHFFFAOYSA-N 2,5-dichloro-4-phenoxyaniline Chemical compound C1=C(Cl)C(N)=CC(Cl)=C1OC1=CC=CC=C1 QXDILMJTDWNTAV-UHFFFAOYSA-N 0.000 description 1
YCJWTHYCBOTYAL-UHFFFAOYSA-N 2,5-dichloro-4-propylaniline Chemical compound CCCC1=CC(Cl)=C(N)C=C1Cl YCJWTHYCBOTYAL-UHFFFAOYSA-N 0.000 description 1
NOLQSBARNJXSOO-UHFFFAOYSA-N 2-benzyl-3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1CC1=CC=CC=C1 NOLQSBARNJXSOO-UHFFFAOYSA-N 0.000 description 1
DWOBGCPUQNFAFB-UHFFFAOYSA-N 2-benzylaniline Chemical compound NC1=CC=CC=C1CC1=CC=CC=C1 DWOBGCPUQNFAFB-UHFFFAOYSA-N 0.000 description 1
FBKQCRAVAOUMHN-UHFFFAOYSA-N 3,4,6-trichloro-2-methoxyaniline Chemical compound COC1=C(N)C(Cl)=CC(Cl)=C1Cl FBKQCRAVAOUMHN-UHFFFAOYSA-N 0.000 description 1
YNMZQQXVRYHMKT-UHFFFAOYSA-N 3,4-dichloro-2-methoxyaniline Chemical compound COC1=C(N)C=CC(Cl)=C1Cl YNMZQQXVRYHMKT-UHFFFAOYSA-N 0.000 description 1
RLTUJGIRWIFRLO-UHFFFAOYSA-N 3,4-dichloro-5-methoxyaniline Chemical compound COC1=CC(N)=CC(Cl)=C1Cl RLTUJGIRWIFRLO-UHFFFAOYSA-N 0.000 description 1
FCNJFFUXQXCKFS-UHFFFAOYSA-N 3,5-dichloro-2-methoxyaniline Chemical compound COC1=C(N)C=C(Cl)C=C1Cl FCNJFFUXQXCKFS-UHFFFAOYSA-N 0.000 description 1
RLECPRVZOAXLMK-UHFFFAOYSA-N 3,5-dichloro-2-phenoxyaniline Chemical compound NC1=CC(Cl)=CC(Cl)=C1OC1=CC=CC=C1 RLECPRVZOAXLMK-UHFFFAOYSA-N 0.000 description 1
GNFMBCBDTFAEHM-UHFFFAOYSA-N 3,5-dichloro-4-methoxyaniline Chemical compound COC1=C(Cl)C=C(N)C=C1Cl GNFMBCBDTFAEHM-UHFFFAOYSA-N 0.000 description 1
GTEUMCIATAHZFK-UHFFFAOYSA-N 3,5-dichloro-4-methylaniline Chemical compound CC1=C(Cl)C=C(N)C=C1Cl GTEUMCIATAHZFK-UHFFFAOYSA-N 0.000 description 1
KFAAKHZTICEVTO-UHFFFAOYSA-N 3,5-dichloro-4-phenoxyaniline Chemical compound ClC1=CC(N)=CC(Cl)=C1OC1=CC=CC=C1 KFAAKHZTICEVTO-UHFFFAOYSA-N 0.000 description 1
DSTYKCDGDXOVOZ-UHFFFAOYSA-N 3,6-dichloro-2-methoxyaniline Chemical compound COC1=C(N)C(Cl)=CC=C1Cl DSTYKCDGDXOVOZ-UHFFFAOYSA-N 0.000 description 1
LTKJFXIFJLXFNJ-UHFFFAOYSA-N 3-benzyl-1,2,5-trichloro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=C(Cl)C=C(Cl)C(Cl)=C1CC1=CC=CC=C1 LTKJFXIFJLXFNJ-UHFFFAOYSA-N 0.000 description 1
VPZJHTWLWKFPQW-UHFFFAOYSA-N 3-chloro-2-methoxyaniline Chemical compound COC1=C(N)C=CC=C1Cl VPZJHTWLWKFPQW-UHFFFAOYSA-N 0.000 description 1
LVFXXXPXOSABGF-UHFFFAOYSA-N 3-chloro-2-phenoxyaniline Chemical compound NC1=CC=CC(Cl)=C1OC1=CC=CC=C1 LVFXXXPXOSABGF-UHFFFAOYSA-N 0.000 description 1
KWTAEBKYISVYFB-UHFFFAOYSA-N 3-chloro-4,5-dimethylaniline Chemical compound CC1=CC(N)=CC(Cl)=C1C KWTAEBKYISVYFB-UHFFFAOYSA-N 0.000 description 1
LBGGMEGRRIBANG-UHFFFAOYSA-N 3-chloro-4-ethylaniline Chemical compound CCC1=CC=C(N)C=C1Cl LBGGMEGRRIBANG-UHFFFAOYSA-N 0.000 description 1
XQVCBOLNTSUFGD-UHFFFAOYSA-N 3-chloro-4-methoxyaniline Chemical compound COC1=CC=C(N)C=C1Cl XQVCBOLNTSUFGD-UHFFFAOYSA-N 0.000 description 1
XLAVBRTYEPFKSD-UHFFFAOYSA-N 3-chloro-5-methoxyaniline Chemical compound COC1=CC(N)=CC(Cl)=C1 XLAVBRTYEPFKSD-UHFFFAOYSA-N 0.000 description 1
XUZCJDBXXYJXDD-UHFFFAOYSA-N 3-chloro-5-methylaniline Chemical compound CC1=CC(N)=CC(Cl)=C1 XUZCJDBXXYJXDD-UHFFFAOYSA-N 0.000 description 1
RQKFYFNZSHWXAW-UHFFFAOYSA-N 3-chloro-p-toluidine Chemical compound CC1=CC=C(N)C=C1Cl RQKFYFNZSHWXAW-UHFFFAOYSA-N 0.000 description 1
OMUPQCXITFAUCB-UHFFFAOYSA-N 4,5-dichloro-2-methoxyaniline Chemical compound COC1=CC(Cl)=C(Cl)C=C1N OMUPQCXITFAUCB-UHFFFAOYSA-N 0.000 description 1
PDOWROQDIXWGIV-UHFFFAOYSA-N 4,5-dichloro-2-phenoxyaniline Chemical compound NC1=CC(Cl)=C(Cl)C=C1OC1=CC=CC=C1 PDOWROQDIXWGIV-UHFFFAOYSA-N 0.000 description 1
WRZOMWDJOLIVQP-UHFFFAOYSA-N 5-Chloro-ortho-toluidine Chemical compound CC1=CC=C(Cl)C=C1N WRZOMWDJOLIVQP-UHFFFAOYSA-N 0.000 description 1
WBSMIPLNPSCJFS-UHFFFAOYSA-N 5-chloro-2-methoxyaniline Chemical compound COC1=CC=C(Cl)C=C1N WBSMIPLNPSCJFS-UHFFFAOYSA-N 0.000 description 1
SXEBHIMOUHBBOS-UHFFFAOYSA-N 5-chloro-2-phenoxyaniline Chemical compound NC1=CC(Cl)=CC=C1OC1=CC=CC=C1 SXEBHIMOUHBBOS-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229910015400 FeC13 Inorganic materials 0.000 description 1
JQGGAELIYHNDQS-UHFFFAOYSA-N Nic 12 Natural products CC(C=CC(=O)C)c1ccc2C3C4OC4C5(O)CC=CC(=O)C5(C)C3CCc2c1 JQGGAELIYHNDQS-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
229910008066 SnC12 Inorganic materials 0.000 description 1
229910008046 SnC14 Inorganic materials 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
230000002950 deficient Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000004673 fluoride salts Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229910052762 osmium Inorganic materials 0.000 description 1
SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
230000002028 premature Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
229910052716 thallium Inorganic materials 0.000 description 1
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/45—Monoamines
- C07C211/46—Aniline
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C209/74—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton by halogenation, hydrohalogenation, dehalogenation, or dehydrohalogenation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA000382858A 1980-08-01 1981-07-30 Process for the preparation of anilines substituted in the meta-position(s) by chlorine Expired CA1211470A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
FR8017324A FR2487823A1 (fr)	1980-08-01	1980-08-01	Procede de preparation selective d'anilines metachlorees
FR8017324		1980-08-01
FR8020979A FR2491059A2 (fr)	1980-09-26	1980-09-26	Procede de preparation selective d'anilines metachlorees
FR8020979		1980-09-26

Publications (1)

Publication Number	Publication Date
CA1211470A true CA1211470A (en)	1986-09-16

Family

ID=26221937

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000382858A Expired CA1211470A (en)	1980-08-01	1981-07-30	Process for the preparation of anilines substituted in the meta-position(s) by chlorine

Country Status (13)

Country	Link
US (1)	US4418213A (da)
EP (1)	EP0045709B1 (da)
KR (1)	KR850000148B1 (da)
BR (1)	BR8104979A (da)
CA (1)	CA1211470A (da)
DD (1)	DD201673A5 (da)
DE (1)	DE3166482D1 (da)
DK (1)	DK342981A (da)
ES (1)	ES8306092A1 (da)
HU (1)	HU187348B (da)
IE (1)	IE51457B1 (da)
IL (1)	IL63297A (da)
SU (1)	SU1176830A3 (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2532305A1 (fr) *	1982-08-24	1984-03-02	Rhone Poulenc Agrochimie	Procede de preparation d'anilines metachlorees
USRE34745E (en) *	1986-10-30	1994-09-27	The Dow Chemical Company	High purity process for the preparation of 4,6-diamino-1,3-benzenediol
US5001279A (en) *	1989-11-17	1991-03-19	The Dow Chemical Company	Aqueous synthesis of 2-halo-4,6-dinitroresorcinol and 4,6-diaminoresorcinol
US5051030A (en) *	1990-06-05	1991-09-24	Roy F. Weston, Inc.	Chemical detoxification process for treatment of soils contaminated with halogenated organic compounds
JPH0565250A (ja) *	1991-01-28	1993-03-19	Ishihara Sangyo Kaisha Ltd	３，５−ジフルオロアニリンの製造方法
US5089653A (en) *	1991-04-04	1992-02-18	Dow Elanco	Process for the selective reduction of the 4-halogen in 2,4-dihaloanilines

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SU517576A1 (ru) *	1971-05-24	1976-06-15	Предприятие П/Я А-7797	Способ получени смешанных галоидароматических углеводородов
DE2503187C3 (de) *	1975-01-27	1979-05-31	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung durch Chlor meta-substituierte Aniline
FR2449075A1 (fr) *	1979-02-15	1980-09-12	Rhone Poulenc Agrochimie	Procede de preparation d'anilines metachlorees
FR2449076A2 (fr) *	1979-02-15	1980-09-12	Rhone Poulenc Agrochimie	Procede de preparation d'anilines metachlorees

1981
- 1981-07-13 IL IL63297A patent/IL63297A/xx unknown
- 1981-07-14 US US06/283,151 patent/US4418213A/en not_active Expired - Fee Related
- 1981-07-30 IE IE1738/81A patent/IE51457B1/en unknown
- 1981-07-30 EP EP81420115A patent/EP0045709B1/fr not_active Expired
- 1981-07-30 DE DE8181420115T patent/DE3166482D1/de not_active Expired
- 1981-07-30 CA CA000382858A patent/CA1211470A/en not_active Expired
- 1981-07-31 BR BR8104979A patent/BR8104979A/pt unknown
- 1981-07-31 DD DD81232269A patent/DD201673A5/de unknown
- 1981-07-31 HU HU812244A patent/HU187348B/hu unknown
- 1981-07-31 ES ES504473A patent/ES8306092A1/es not_active Expired
- 1981-07-31 DK DK342981A patent/DK342981A/da not_active Application Discontinuation
- 1981-08-01 KR KR1019810002798A patent/KR850000148B1/ko not_active Expired
- 1981-08-01 SU SU813316601A patent/SU1176830A3/ru active

Also Published As

Publication number	Publication date
IL63297A0 (en)	1981-10-30
US4418213A (en)	1983-11-29
EP0045709B1 (fr)	1984-10-03
EP0045709A1 (fr)	1982-02-10
IE811738L (en)	1982-02-01
DD201673A5 (de)	1983-08-03
SU1176830A3 (ru)	1985-08-30
KR850000148B1 (ko)	1985-02-28
IL63297A (en)	1984-05-31
DE3166482D1 (en)	1984-11-08
DK342981A (da)	1982-02-02
ES504473A0 (es)	1982-12-01
IE51457B1 (en)	1986-12-24
HU187348B (en)	1985-12-28
KR830006170A (ko)	1983-09-17
BR8104979A (pt)	1982-04-20
ES8306092A1 (es)	1982-12-01

Legal Events

Date	Code	Title	Description
2003-09-16	MKEX	Expiry

Publication	Publication Date	Title
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